US8993754B2 - Iridium complex and light emitting material formed from same - Google Patents

Iridium complex and light emitting material formed from same Download PDF

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US8993754B2
US8993754B2 US13/392,402 US201013392402A US8993754B2 US 8993754 B2 US8993754 B2 US 8993754B2 US 201013392402 A US201013392402 A US 201013392402A US 8993754 B2 US8993754 B2 US 8993754B2
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Hideo Konno
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National Institute of Advanced Industrial Science and Technology AIST
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H01L51/0085—
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H01L51/5016—
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to an iridium complex useful as materials for organic electroluminescent elements, electrochemiluminescence (ECL) element materials, luminescent sensors, oxygen sensor, photosensitizers, displays, materials for photographs, laser dyes, dyes for color filters, optical communications, color conversion filters, backlights, illumination, photosensitizing dyes, luminescent probes for cell imaging, various light sources, etc., and a luminescent material comprising the compound.
  • ECL electrochemiluminescence
  • Organic electroluminescent elements have received attention as next-generation display elements, and the development of various organic materials used in the luminescent elements has been promoted actively in recent years. Particularly, attention has been focused on phosphorescent materials that utilize luminescence from an excited triplet state, as luminescent materials from the viewpoint of improvement in luminous efficiency.
  • the limit of external quantum efficiency is allegedly 5% because the generation ratio between a singlet exciton and a triplet exciton is 1:3 and thus the generation probability of luminescent excited species is 25% and because light extraction efficiency is approximately 20%.
  • luminous efficiency becomes four times in principle compared with the case of the excited singlet because the upper limit of internal quantum efficiency becomes 100%; thus the development of phosphorescent materials has been performed actively.
  • iridium complexes having a 2-phenylpyridine-based ligand have received attention so far as typical phosphorescent materials, the development of novel phosphorescent materials has been demanded with the future objective of further improvement in luminous efficiency and durability.
  • Iridium complexes having a 2-phenylpyrimidine-based ligand similar to a compound of the present invention are described in Patent Literatures 1 to 7 and Non Patent Literatures 1 to 3.
  • the problems to be solved such as luminous efficiency or durability, still remain, and more thermally stable materials exhibiting high luminous efficiency have been demanded.
  • Non Patent Literature 2 An iridium complex in which a phenyl group or a thienyl group is introduced in position 5 of the pyrimidine ring of a 2-phenylpyrimidine ligand (e.g., formula (B)) is disclosed in Non Patent Literature 2.
  • the emission wavelengths of these iridium complexes are 522 to 558 nm and their colors of luminescence are limited to green to orange regions.
  • the iridium complex of the skeleton described in Non Patent Literature 2 it is difficult to emit light in a blue region.
  • the emission quantum yields of these iridium complexes in toluene are 0.052 to 0.34 and are still low.
  • Patent Literature 7 An iridium complex in which a methyl group is introduced in position 4 of the pyrimidine ring of a 2-phenylpyrimidine ligand (formula (C)) is disclosed in Patent Literature 7.
  • a methyl group is introduced in position 4 of the pyrimidine ring of a 2-phenylpyrimidine ligand (formula (C))
  • Patent Literature 7 An iridium complex in which a methyl group is introduced in position 4 of the pyrimidine ring of a 2-phenylpyrimidine ligand (formula (C)) is disclosed in Patent Literature 7.
  • isomers are generated depending on coordination patterns to iridium (see a diagram below), and there are problems: it is difficult to synthesize the intended iridium complex with high purity. Also, there is the possibility that contamination with various isomers have adverse effect on luminescent elements.
  • phosphorescent materials exhibiting a high emission quantum yield in a solid state are preferable for solid devices such as organic electroluminescent elements, and further, phosphorescent materials highly soluble in a solvent have been desired strongly in the case of producing films of these phosphorescent materials by a coating method.
  • the 2-phenylpyrimidine-based iridium complexes described in Patent Literatures 1 to 7 and Non Patent Literatures 1 to 3 still have room for improvement from the viewpoints described above.
  • An object of the present invention is to provide a luminescent element capable of luminescence with high brightness/high efficiency and excellent in durability, and a novel iridium complex that can be used in the luminescent element and can also be applied to organic electroluminescent element materials, electrochemiluminescence (ECL) element materials, luminescent sensors, oxygen sensors, photosensitizers, displays, materials for photographs, laser dyes, dyes for color filters, optical communications, color conversion filters, backlights, illumination, photosensitizing dyes, luminescent probes for cell imaging, various light sources, etc.
  • ECL electrochemiluminescence
  • a novel iridium complex represented by formula (1) or (2) is very thermally stable compared with conventional compounds in which a substituent is not introduced in R a , has excellent luminescence properties, particularly in a solid state, in the visible light region, is further highly soluble in a solvent and excellent in workability, and is useful as luminescent materials for various applications.
  • N represents a nitrogen atom
  • R a represents an alkyl group having 2 to 30 carbon atoms which may have a substituent
  • R 1 to R 4 each independently represent a hydrogen atom or an alkyl group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 60 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, an alkynyl group having 2 to 30 carbon atoms which may have a substituent, an amino group having 0 to 30 carbon atoms which may have a substituent, a heterocyclic group having 1 to 60 carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an alkylthio group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 60 carbon atoms which may have a substituent, an arylthio group having 6 to
  • N represents a nitrogen atom
  • m represents an integer of 1 to 3
  • n represents an integer of 0 to 2
  • m+n 3
  • R a represents an alkyl group having 2 to 30 carbon atoms which may have a substituent
  • R 1 to R 4 each independently represent a hydrogen atom or an alkyl group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 60 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, an alkynyl group having 2 to 30 carbon atoms which may have a substituent, an amino group having 0 to 30 carbon atoms which may have a substituent, a heterocyclic group having 1 to 60 carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an alkylthio group having 1 to 30 carbon atoms which may have a substituent, an
  • R 5 to R 76 each independently represent a hydrogen atom or an alkyl group having 1 to 30 carbon atoms which may have a substituent, an aryl group having 6 to 60 carbon atoms which may have a substituent, an alkenyl group having 2 to 30 carbon atoms which may have a substituent, an alkynyl group having 2 to 30 carbon atoms which may have a substituent, an amino group having 0 to 30 carbon atoms which may have a substituent, a heterocyclic group having 1 to 60 carbon atoms which may have a substituent, an alkoxy group having 1 to 30 carbon atoms which may have a substituent, an alkylthio group having 1 to 30 carbon atoms which may have a substituent, an aryloxy group having 6 to 60 carbon atoms which may have a substituent, an arylthio group having 6 to 60 carbon atoms which may have a substituent, a heterocyclic oxy group having 1 to 60 carbon atoms which may have a
  • a luminescent element using the compound is suitable for fields such as display elements, displays, backlights, electrophotography, illumination light sources, recording light sources, exposing light sources, readout light sources, signs, sigh boards, and interiors.
  • the iridium complex of the present invention can also be applied to medical use, oxygen sensors, materials for photographs, UV absorbing materials, laser dyes, dyes for color filters, color conversion filters, luminescent probes for cell imaging, optical communications, etc.
  • FIG. 1 It is the luminescence spectrum of compound (43) of the present invention in THF at room temperature under an argon atmosphere. Excitation light is 350 nm.
  • FIG. 2 It is the luminescence spectrum of compound (53) of the present invention in THF at room temperature under an argon atmosphere. Excitation light is 350 nm.
  • FIG. 3 It is the luminescence spectrum of compound (82) of the present invention in THF at room temperature under an argon atmosphere. Excitation light is 350 nm.
  • An iridium complex according to the present invention has a substructure represented by formula (1) and, preferably, is represented by formula (2), and a luminescent element exhibiting excellent luminescence in the visible light region is obtained by allowing these iridium complexes to be contained in a luminescent layer or a plurality of organic compound layers including a luminescent layer in the luminescent element.
  • the iridium complex according to the present invention is characterized by having a 2-phenylpyrimidine-based ligand of a particular structure.
  • the present inventor has found that the thermal stability and, particularly the emission quantum yield in a solid state, of the iridium complex largely increase by introducing an alkyl group having 2 to 30 carbon atoms which may have a substituent in R a described in formula (1) or (2).
  • the 2-phenylpyrimidine-based ligand and iridium which is a central metal, form a bond, intersystem crossing from an excited singlet state to an excited triplet state is promoted by heavy atom effect and as a result, the iridium complex of the present invention efficiently exhibits phosphorescence emission in the visible light region.
  • the iridium complex according to the present invention may contain an isomer (e.g., facial forms, meridional forms, and isomers described in Japanese Patent Application Laid-Open Publication No. 2006-278781 or Japanese Patent Application Laid-Open Publication No. 2008-288254).
  • an isomer e.g., facial forms, meridional forms, and isomers described in Japanese Patent Application Laid-Open Publication No. 2006-278781 or Japanese Patent Application Laid-Open Publication No. 2008-288254.
  • the iridium complex according to the present invention is neutral or ionic, more preferably neutral or cationic, particularly preferably a neutral iridium complex.
  • the emission quantum yield in a solution under air, under an inert gas atmosphere, or under deaeration, preferably under in an inert gas atmosphere or under deaeration
  • the emission quantum yield in a solution under air, under an inert gas atmosphere, or under deaeration, preferably under in an inert gas atmosphere or under deaeration
  • it is 0.1 or more is more preferable
  • one in which it is 0.4 or more is particularly preferable
  • one in which it is 0.5 or more is most preferable.
  • the emission quantum yield in a solid state is 0.01 or more is preferable, one in which it is 0.05 or more is more preferable, one in which it is 0.1 or more is particularly preferable, and one in which it is 0.3 or more is most preferable.
  • the emission quantum yield in a solid state is a value determined by directly irradiating the iridium complex in a solid state with excitation light without doping with a host material or the like and measuring the luminescence.
  • the measurement of the emission quantum yield in a solution should be performed after aerating inert gas (argon gas or nitrogen gas) to a solution in which the iridium complex is dissolved or should be performed after freezing/deaerating a solution in which the iridium complex is dissolved.
  • aerating inert gas argon gas or nitrogen gas
  • Any of an absolute method and a relative method may be used as a measurement method for the emission quantum yield.
  • the relative method can measure the emission quantum yield by the comparison of a luminescence spectrum with a reference substance (kinin sulfate, etc.).
  • the measurement of the emission quantum yield in a solution or in a solid state is possible by using a commercially available apparatus (absolute PL quantum yield measurement apparatus (C9920) manufactured by Hamamatsu Photonics K.K.).
  • a commercially available apparatus absolute PL quantum yield measurement apparatus (C9920) manufactured by Hamamatsu Photonics K.K.
  • the emission quantum yield in a solution can be measured using various solvents
  • the iridium complex according to the present invention needs only to achieve the emission quantum yield described above in any of arbitrary solvents.
  • the emission maximum wavelength of a luminescence spectrum in a solution or in a solid state is in the range of 300 nm to 900 nm is preferable, and one in which it is in the range of 400 nm to 800 nm is more preferable.
  • trivalence or tetravalence is preferable, and trivalence is more preferable.
  • n represents an integer of 0 to 2
  • m+n 3.
  • Q represents a counter ion.
  • a counter ion which is however, for example, an alkali metal ion, an alkaline earth metal ion, a halogen ion, a perchlorate ion, a PF 6 ion, an ammonium ion, a CF 3 CF 2 CF 2 COO ion, a SbF 6 ion, a dicyanamide ion, a bis(trifluoromethanesulfonyl)amide ion, a borate ion, a trifluoroacetic acid ion, a trifluoromethanesulfonate ion, a phosphonium ion, or a tetrakis[3,5-bis(trifluoromethyl)phenyl]borate ion, and one that is preferred is a halogen ion, a perchlorate ion, a PF 6 ion,
  • k represents an integer of 0 to 2. k is preferably 0 or 1, more preferably 0.
  • L is a bidentate ligand, a neutral bidentate ligand or anionic bidentate ligand is preferable, and an anionic bidentate ligand is more preferable, with a monoanionic bidentate ligand particularly preferred.
  • L should be a bidentate ligand forming a Ir-nitrogen bond and a Ir-carbon bond, a bidentate ligand forming a Ir-nitrogen bond and a Ir-oxygen bond, a bidentate ligand forming two Ir-oxygen bonds, or a bidentate ligand forming two Ir-nitrogen bonds.
  • the bidentate ligand forming a Ir-nitrogen bond and a Ir-carbon bond is, for example, a 2-phenylpyridine derivative, a 2-phenylpyrimidine derivative, a 2-phenylquinoline derivative, a 1-phenylisoquinoline derivative, a 3-phenylisoquinoline derivative, a 2-(2-benzothiophenyl)pyridine derivative, a 2-thienylpyridine derivative, a 1-phenylpyrazole derivative, a 1-phenyl-1H-indazole derivative, a 2-phenylbenzothiazole derivative, a 2-phenylthiazole derivative, a 2-phenylbenzoxazole derivative, a 2-phenyloxazole derivative, a 2-furanylpyridine derivative, a 2-(2-benzofuranyl)pyridine derivative, a 7,8-benzoquinoline derivative, a 7,8-benzoquinoxaline derivative, a dibenzo[f,h]quinoline derivative, a dibenzo
  • Japanese Patent Application Laid-Open Publication No. 2005-2978 Japanese Patent Application Laid-Open Publication No. 2005-29784, Japanese Patent Application Laid-Open Publication No. 2005-29783, Japanese Patent Application Laid-Open Publication No. 2005-29782, Japanese Patent Application Laid-Open Publication No. 2005-23072, Japanese Patent Application Laid-Open Publication No. 2005-23071, Japanese Patent Application Laid-Open Publication No. 2005-23070, Japanese Patent Application Laid-Open Publication No. 2005-2101, Japanese Patent Application Laid-Open Publication No. 2005-2053, Japanese Patent Application Laid-Open Publication No. 2005-78996, Japanese Patent Application Laid-Open Publication No. 2005-68110, Japanese Patent Application Laid-Open Publication No.
  • R in Table 1 to Table 2 is a hydrogen atom or a substituent, and the desirable range is the same as R 1 to R 76 described later.
  • * in Table 1 and Table 2 represents a binding site for iridium.
  • the bidentate ligand forming a Ir-nitrogen bond and a Ir-oxygen bond is, for example, a picolinic acid derivative, a pyridinesulfonic acid derivative, a quinolinesulfonic acid derivative, or a quinolinecarboxylic acid derivative, and a picolinic acid derivative is preferable.
  • a picolinic acid derivative for example, a picolinic acid derivative, a pyridinesulfonic acid derivative, a quinolinesulfonic acid derivative, or a quinolinecarboxylic acid derivative, and a picolinic acid derivative is preferable.
  • Japanese Patent Application Laid-Open Publication No. 2006-16394 Japanese Patent Application Laid-Open Publication No. 2006-307210
  • Japanese Patent Application Laid-Open Publication No. 2006-298900 International Publication No. WO2006-028224
  • International Publication No. WO2006-097717 Japanese Patent Application Laid-Open Publication No. 2004-111379
  • the bidentate ligand forming two Ir-oxygen bonds is, for example, a ⁇ -diketone derivative, a carboxylic acid derivative, or a tropolone derivative, and a ⁇ -diketone derivative is preferable.
  • a ⁇ -diketone derivative is preferable.
  • Japanese Patent Application Laid-Open Publication No. 2005-35902 Japanese Patent Application Laid-Open Publication No. 2004-349224, Japanese Patent Application Laid-Open Publication No. 2006-28101, Japanese Patent Application Laid-Open Publication No. 2005-29785, etc.
  • the bidentate ligand forming two Ir-nitrogen bonds is, for example, a 2,2′-bipyridine derivative, a 1,10-phenanthroline derivative, a 2,2′-biquinoline derivative, a 2,2′-dipyridylamine derivative, an imidazole derivative, a pyrazolylborate derivative, or a pyrazole derivative.
  • a 2,2′-bipyridine derivative for example, a 1,10-phenanthroline derivative, a 2,2′-biquinoline derivative, a 2,2′-dipyridylamine derivative, an imidazole derivative, a pyrazolylborate derivative, or a pyrazole derivative.
  • a structure particularly preferable as L is shown in formulas (3) to (11). Specifically, the monoanionic bidentate ligand is (3) to (6), (10), or (11), and the neutral bidentate ligand is (7) to (9).
  • R a is an alkyl group having 2 to 30 carbon atoms (preferably 2 to 20 carbon atoms, more preferably 3 to 20 carbon atoms, particularly preferably 5 to 20 carbon atoms, most preferably 10 to 20 carbon atoms) which may have a substituent.
  • a case in which the alkyl group having 2 to 30 carbon atoms which may have a substituent is introduced in R a is preferable and very preferable, particularly from the viewpoint of luminescent element preparation using a coating process, because the solubility of the iridium complex, which is the compound of the present invention, in a solvent (dichloromethane, chloroform, toluene, THF, xylene, etc.) largely increases, improving the operability of synthesis or purification.
  • alkyl group which may have a substituent examples include an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, a neopentyl
  • one that is preferred includes an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, an n-nonyl group, an n-decyl group, an n-undecyl group, an n-dodecyl group, an n-tridecyl group, an n-tetradecyl group, an n-pentadecyl group, an n-hexadecyl group, an n-heptadecyl group, an n-octadecyl group, a neopentyl group, a 1-methylpentyl group, a 1-pentyl group,
  • R 1 to R 76 each independently represent a hydrogen atom or an alkyl group having 1 to 30 carbon atoms (preferably 1 to 20 carbon atoms, more preferably 1 to 15 carbon atoms, particularly preferably 1 to 10 carbon atoms, most preferably 1 to 5 carbon atoms) which may have a substituent, an aryl group having 6 to 60 carbon atoms (preferably 6 to 30 carbon atoms, more preferably 6 to 20 carbon atoms, particularly preferably 6 to 15 carbon atoms, most preferably 6 to 12 carbon atoms) which may have a substituent, an alkenyl group having 2 to 30 carbon atoms (preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 15 carbon atoms, most preferably 2 to 10 carbon atoms) which may have a substituent, an alkynyl group having 2 to 30 carbon atoms (preferably 2 to 30 carbon atoms, more preferably 2 to 20 carbon atoms, particularly preferably 2 to 10 carbon atoms
  • alkyl group having 1 to 30 carbon atoms which may have a substituent examples include a methyl group which may have a substituent and the alkyl groups having 2 to 30 carbon atoms which may have a substituent exemplified in the description of R a .
  • Examples of the aryl group having 6 to 60 carbon atoms which may have a substituent include a phenyl group, a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, a p-terphenyl-4-yl group, a p-terphenyl-3-yl group, a p-terphenyl-2-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, an o-tolyl group, an m-tolyl group, a p-tolyl group, a p-t-butylphenyl group, a p-(2-phenylpropyl)phenyl group, a 4′-methylbiphenylyl group, a 4′′-t-butyl-p-terphenyl-4-yl group, an
  • a phenyl group a biphenyl-2-yl group, a biphenyl-3-yl group, a biphenyl-4-yl group, an m-terphenyl-4-yl group, an m-terphenyl-3-yl group, an m-terphenyl-2-yl group, a p-tolyl group, a 3,4-xylyl group, or an m-quaterphenyl-2-yl group, and one that is particularly preferred is a phenyl group, wherein these aryl groups may have a substituent.
  • dendron residues of the following formula described in Japanese Patent Application Laid-Open Publication No. 2009-149617 are included:
  • R e represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, and some of hydrogen atoms in these substituents may be substituted by halogen atoms.
  • a plurality of R e s present may be the same or different, provided that at least one of R e s is an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms.
  • R f represents a linear or branched alkyl group having 1 to 10 carbon atoms. A plurality of R f s present may be the same or different.
  • * represents a binding site for le to R 76 above.
  • Diynyl groups such as a 1,3-butadiynyl group are also included in such an alkynyl group.
  • amino group which may have a substituent examples include an amino group, a dibenzylamino group, a ditolylamino group, a methylamino group, a dimethylamino group, an ethylamino group, a diethylamino group, an n-propylamino group, a di-n-propylamino group, an isopropylamino group, a diisopropylamino group, an n-butylamino group, an s-butylamino group, an isobutylamino group, a t-butylamino group, an n-pentylamino group, an n-hexylamino group, a cyclohexylamino group, an n-heptylamino group, an n-octylamino group, a 2-ethylhexylamino group, an n-nonylamino group, an
  • one that is preferred includes a 2-pyridinyl group, a 1-indolizinyl group, a 2-indolizinyl group, a 3-indolizinyl group, a 5-indolizinyl group, a 6-indolizinyl group, a 7-indolizinyl group, a 8-indolizinyl group, a 2-imidazopyridinyl group, a 3-imidazopyridinyl group, a 5-imidazopyridinyl group, a 6-imidazopyridinyl group, a 7-imidazopyridinyl group, a 8-imidazopyridinyl group, a 3-pyridinyl group, a 4-pyridinyl group, a 1-indolyl group, a 2-indolyl group, a 3-indolyl group, a 4-indolyl group, a 5-indolyl group, a 6-indolyl group,
  • the alkoxy group or alkylthio group which may have a substituent is a group represented by —OY or —SY, and examples of Y include a methyl group, an ethyl group, a propyl group, an isopropyl group, an n-butyl group, an s-butyl group, an isobutyl group, a t-butyl group, an n-pentyl group, an n-hexyl group, an n-heptyl group, an n-octyl group, a hydroxymethyl group, a 1-hydroxyethyl group, a 2-hydroxyethyl group, a 2-hydroxyisobutyl group, a 1,2-dihydroxyethyl group, a 1,3-dihydroxyisopropyl group, a 2,3-dihydroxy-t-butyl group, a 1,2,3-trihydroxypropyl group, a chloromethyl group, a 1-chlor
  • the aryloxy group or arylthio group which may have a substituent is a group represented by —OZ or —SZ, and examples of Z include a phenyl group, C 1 to C 12 alkoxyphenyl groups, C 1 to C 12 alkylphenyl groups, a 1-naphthyl group, a 2-naphthyl group, and a pentafluorophenyl group.
  • R e represents a hydrogen atom, an alkyl group having 1 to 10 carbon atoms, or an alkoxy group having 1 to 10 carbon atoms, and some of hydrogen atoms in these substituents may be substituted by halogen atoms.
  • a plurality of R e s present may be the same or different, provided that at least one of R e s is an alkyl group having 1 to 10 carbon atoms or an alkoxy group having 1 to 10 carbon atoms.
  • * represents a binding site for R 1 to R 76 above.
  • the heterocyclic oxy group or heterocyclic thio group which may have a substituent is a group represented by —OHet or —SHet
  • examples of Het include a thienyl group, C 1 to C 12 alkoxythienyl groups, C 1 to C 12 alkylthienyl groups, a pyrrolyl group, C 1 to C 12 alkoxypyrrolyl groups, C 1 to C 12 alkylpyrrolyl group, a furyl group, C 1 to C 12 alkoxyfuryl groups, C 1 to C 12 alkylfuryl group, a pyridinyl group, C 1 to C 12 alkoxypyridinyl groups, C 1 to C 12 alkylpyridinyl group, a piperidinyl group, C 1 to C 12 alkoxypiperidinyl groups, C 1 to C 12 alkylpiperidinyl groups, a quinolyl group, and an isoquinolyl group.
  • acyl groups include an acetyl group, propionyl group, a butyryl group, an isobutyryl group, a pivaloyl group, a benzoyl group, a trifluoroacetyl group, and a pentafluorobenzoyl group.
  • acyloxy group The number of carbon atoms in the acyloxy group described above is usually on the order of 2 to 20, with 2 to 18 preferred.
  • Specific acyloxy groups include an acetoxy group, a propionyloxy group, a butyryloxy group, an isobutyryloxy group, a pivaloyloxy group, a benzoyloxy group, a trifluoroacetyloxy group, and a pentafluorobenzoyloxy group.
  • substituted silyl group, substituted silyloxy group, substituted silylthio group, and substituted silylamino group described above include those in which the substituted silyl moiety is a triethylsilyl group, a triisopropylsilyl group, a t-butyldimethylsilyl group, or a t-butyldiphenylsilyl group.
  • alkyl group of R a and the alkyl group, aryl group, alkenyl group, alkynyl group, amino group, heterocyclic group, alkoxy group, alkylthio group, aryloxy group, arylthio group, heterocyclic oxy group, and heterocyclic thio group of R 1 to R 76 described above may have includes, in addition to those described above, further: alkyl groups such as a methyl group, an ethyl group, a propyl group, and a t-butyl group; aralkyl groups such as a benzyl group and a phenethyl group; alkoxyl groups such as a methoxyl group, an ethoxyl group, and a propoxyl group; aryl groups such as a phenyl group and a biphenyl group; heterocyclic groups such as a thienyl group, a pyrrolyl group, and a pyri
  • R 1 to R 76 will be described further specifically.
  • a hydrogen atom, a halogen atom, an aryl group having 6 to 30 carbon atoms which may have a substituent, or an alkyl group having 1 to 20 carbon atoms which may have a substituent is more preferable as R 1
  • a hydrogen atom, a fluorine atom, an aryl group having 6 to 12 carbon atoms which may have a substituent, or an alkyl group having 1 to 10 carbon atoms which may have a substituent is particularly preferable, with a hydrogen atom or a fluorine atom most preferred.
  • a hydrogen atom, a halogen atom, a trifluoromethyl group, a cyano group, an aryl group having 6 to 30 carbon atoms which may have a substituent, or an alkyl group having 1 to 20 carbon atoms which may have a substituent is more preferable as R 2
  • a hydrogen atom, a trifluoromethyl group, an aryl group having 6 to 12 carbon atoms which may have a substituent, or an alkyl group having 1 to 10 carbon atoms which may have a substituent is particularly preferable.
  • a hydrogen atom, a halogen atom, an aryl group having 6 to 30 carbon atoms which may have a substituent, or an alkyl group having 1 to 20 carbon atoms which may have a substituent is more preferable as R 3
  • a hydrogen atom, a fluorine atom, an aryl group having 6 to 12 carbon atoms which may have a substituent, or an alkyl group having 1 to 10 carbon atoms which may have a substituent is particularly preferable.
  • a hydrogen atom, a trifluoromethyl group, or an alkyl group having 1 to 10 carbon atoms which may have a substituent is more preferable as R 4
  • a hydrogen atom or an alkyl group having 1 to 5 carbon atoms which may have a substituent is particularly preferable, with a hydrogen atom most preferred.
  • a trifluoromethyl group, an aryl group having 6 to 12 carbon atoms which may have a substituent, or an alkyl group having 1 to 10 carbon atoms which may have a substituent is more preferable as R 13 and R 15 , and an alkyl group having 1 to 5 carbon atoms which may have a substituent is particularly preferable, with an alkyl group having 1 to 3 carbon atoms which may have a substituent most preferred.
  • a hydrogen atom or an alkyl group having 1 to 10 carbon atoms which may have a substituent is more preferable as R 14 and R 20 to R 31
  • a hydrogen atom or an alkyl group having 1 to 5 carbon atoms which may have a substituent is particularly preferable, with a hydrogen atom most preferred.
  • a hydrogen atom, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, or a heterocyclic group having 1 to 20 carbon atoms which may have a substituent is more preferable as R 52
  • a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aryl group having 6 to 12 carbon atoms which may have a substituent is particularly preferable.
  • a hydrogen atom, a halogen atom, a trifluoromethyl group, a cyano group, a carboxyl group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, or a heterocyclic group having 1 to 20 carbon atoms which may have a substituent is more preferable as R 5 to R 12 , R 16 to R 19 , R 32 to R 51 , R 53 to R 58 , R 60 to R 62 , and R 64 to R 76 , and a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aryl group having 6 to 12 carbon atoms which may have a substituent is particularly preferable.
  • a hydrogen atom, a halogen atom, a trifluoromethyl group, a cyano group, a carboxyl group, an alkyl group having 1 to 20 carbon atoms which may have a substituent, an aryl group having 6 to 30 carbon atoms which may have a substituent, or a heterocyclic group having 1 to 20 carbon atoms which may have a substituent is more preferable as R 59 and R 63
  • a hydrogen atom, an alkyl group having 1 to 10 carbon atoms which may have a substituent, or an aryl group having 6 to 12 carbon atoms which may have a substituent is particularly preferable, with an alkyl group having 1 to 5 carbon atoms which may have a substituent most preferred.
  • R 1 to R 76 should be bonded to each other to form a saturated or unsaturated carbon ring or a saturated or unsaturated heterocyclic ring.
  • R 1 to R 3 should be bonded to form a naphthalene skeleton or acenaphthene skeleton as in the following formula.
  • R b is a hydrogen atom or a substituent, and the desirable range is also the same as R 1 to R 76 .
  • R 2 is an aryl group which may have a substituent
  • the iridium complex according to the present invention it has been revealed that it exhibits a high emission quantum yield, particularly in a solid state.
  • the present inventor has assumed as to its reason that the alkyl group having 2 to 30 carbon atoms which may have a substituent is introduced at the particular site R a , whereby the influence of concentration quenching decreases, resulting in strong luminescence even in a solid state.
  • L does not directly contribute to the luminescence properties of a metal complex but may slightly change the luminescence properties, and it is called an ancillary ligand (see e.g., Japanese Unexamined Patent Application Publication No. 2006-513278).
  • the 2-phenylpyrimidine-based ligand described in formula (1) or (2) principally contributes to the luminescence properties of the iridium complex of the present invention, as described above.
  • its emission wavelength can be changed according to application by combining the bidentate ligand with the conventionally known ancillary ligand described in the prior document.
  • the emission wavelength of the metal complex of the present invention by a method of introducing a substituent to R 1 to R 4 .
  • a substituent to R 1 to R 4 For example, luminescence shifts toward short wavelengths by introducing a fluorine atom to R 1 or R 3 .
  • These iridium complexes can be used preferably as blue luminescent materials.
  • iridium complexes represented by formula (1) iridium complexes represented by formulas (12) to (20) are particularly preferable.
  • iridium complexes represented by formula (2) it is also preferred to have the iridium complexes represented by formulas (12) to (20) as a substructure.
  • R c is a hydrogen atom or a substituent, and the desirable range is also the same as R 1 to R 76 .
  • a one-step method of reacting iridium trichloride or iridium trisacetylacetonate with a 2-phenylpyrimidine-based ligand a two-step method of first synthesizing a chlorine-bridged dimer by reacting iridium trichloride with a 2-phenylpyrimidine-based ligand, and reacting this with the ligand L, etc.
  • heating means is not particularly limited, irradiation with microwave is also preferable for smoothly promoting the reactions.
  • the wavelength of the microwave which is however 2000 to 3000 MHz, and one that is preferred is 2400 to 2500 MHz.
  • Every commercially available reaction apparatus for organic synthesis or the like can be applied as a microwave oscillation apparatus.
  • an oil bath, mantle heater, or the like may be used as heating means.
  • reaction solvent for further smoothly promoting the reaction that synthesizes the iridium complex according to the present invention, it is desirable to use a reaction solvent.
  • a solvent an alcoholic solvent, protic solvent, aprotic solvent, nitrile-based solvent, or the like is preferably used.
  • the reaction temperature, the reaction pressure and the reaction time differ depending on the raw material used, the solvent, etc., usually the reaction temperature is 40 to 250° C., preferably 50 to 230° C., more preferably 60 to 220° C. and the reaction pressure is 1 to 30 atm, preferably 1 to 5 atm.
  • the iridium complex according to the present invention can be treated according to the usual posttreatment of synthesis reaction and then used, if necessary after being purified, or without being purified.
  • a method of the posttreatment for example, extraction, cooling, crystallization by adding water or an organic solvent, an operation of distilling off the solvent from the reaction mixture, and so on can be performed alone or in combination.
  • a method of the purification recrystallization, distillation, sublimation, column chromatography, and so on can be performed alone or in combination.
  • —C 3 H 7 , —C 4 H 9 , —C 5 H 11 , —C 7 H 15 , —C 8 H 17 , —C 9 H 19 , —C 10 H 21 , —C 12 H 25 , —C 15 H 31 , and —C 18 H 37 described in Table 3 to Table 12 each represent a linear alkyl group, and —OC 6 H 13 and —OC 7 H 15 each represent a linear alkoxy group.
  • the organic layer was separated/collected and separated/purified by silica gel chromatography (eluent: a mixed solvent of dichloromethane and hexane) to obtain 4.1 g of compound A.
  • silica gel chromatography eluent: a mixed solvent of dichloromethane and hexane
  • the 1 H-NMR data of the compound A is shown below.
  • the organic layer was separated/collected and separated/purified by silica gel chromatography (eluent: a mixed solvent of dichloromethane and hexane) to obtain 2.50 g of compound B.
  • silica gel chromatography eluent: a mixed solvent of dichloromethane and hexane
  • the 1 H-NMR data of the compound B is shown below.
  • the organic layer was separated/collected and separated/purified by silica gel chromatography (eluent: a mixed solvent of dichloromethane and hexane) to obtain 2.52 g of compound C.
  • silica gel chromatography eluent: a mixed solvent of dichloromethane and hexane
  • the 1 H-NMR data of the compound C is shown below.
  • the organic layer was separated/collected and separated/purified by silica gel chromatography (eluent: a mixed solvent of dichloromethane and hexane) to obtain compound G.
  • the isolation yield was 67%.
  • the 1 H-NMR data of the compound G is shown below.
  • the deposited solid was separated/purified by silica gel chromatography (eluent: a mixed solvent of dichloromethane and hexane) to obtain compound (12) of the present invention at an isolation yield of 40%. Meridional forms and facial forms were obtained.
  • the 1 H-NMR data of the compound (12) of the present invention is shown below.
  • the organic layer was separated/collected and separated/purified by silica gel chromatography (eluent: a mixed solvent of dichloromethane and hexane) to obtain 2.57 g of compound L.
  • silica gel chromatography eluent: a mixed solvent of dichloromethane and hexane
  • the 1 H-NMR data of the compound L is shown below.
  • Solid obtained by concentrating the filtrate was separated/purified by silica gel chromatography (eluent: a mixed solvent of dichloromethane and hexane) to obtain 1.08 g of an intermediate.
  • 1 g of the intermediate obtained by the operation described above 47.3 mg of 2,4-difluorophenylboronic acid, 10 mL of 1,2-dimethoxyethane, and 9 ml of a 2 M aqueous solution of potassium carbonate were placed in a two-neck flask. After argon gas was aerated into this solution for 20 minutes, 15.8 mg of a tetrakistriphenylphosphine (0) palladium complex was placed therein.
  • the organic layer was separated/collected and separated/purified by silica gel chromatography (eluent: a mixed solvent of dichloromethane and hexane) to obtain 2.13 g of an intermediate.
  • 2.13 g of the intermediate obtained by the operation described above, 3.53 g of (3,5-diphenylphenyl)boronic acid, 34 ml of toluene, 3.16 g of K 3 PO 4 , 118 mg of Pd 2 (dba) 3 , and 212 mg of 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl were placed in a two-neck flask and heated to reflux for 17 hours under an argon atmosphere.
  • reaction solution was cooled to room temperature and then filtered through a celite layer. Solid obtained by concentrating the filtrate was separated/purified by silica gel chromatography (eluent: a mixed solvent of dichloromethane and hexane) to obtain 0.81 g of compound P.
  • silica gel chromatography eluent: a mixed solvent of dichloromethane and hexane
  • the emission quantum yield (excitation wavelength: 350 nm) of the compound (12) of the present invention in a solid state at room temperature using an absolute PL quantum yield measurement apparatus (C9920) manufactured by Hamamatsu Photonics K.K.
  • the emission quantum yield was 0.14.
  • the emission quantum yield (excitation wavelength: 350 nm) of the compound (47) of the present invention in a solid state at room temperature using an absolute PL quantum yield measurement apparatus (C9920) manufactured by Hamamatsu Photonics K.K., the emission quantum yield was 0.12.
  • the emission quantum yield (excitation wavelength: 350 nm) of the compound (75) of the present invention in a solid state at room temperature using an absolute PL quantum yield measurement apparatus (C9920) manufactured by Hamamatsu Photonics K.K.
  • the emission quantum yield was 0.22.
  • the emission quantum yield (excitation wavelength: 350 nm) of the compound (76) of the present invention in a solid state at room temperature using an absolute PL quantum yield measurement apparatus (C9920) manufactured by Hamamatsu Photonics K.K.
  • the emission quantum yield was 0.18.
  • the emission quantum yield (excitation wavelength: 350 nm) of the compound (82) of the present invention in a solid state at room temperature using an absolute PL quantum yield measurement apparatus (C9920) manufactured by Hamamatsu Photonics K.K.
  • the emission quantum yield was 0.34.
  • the emission quantum yield (excitation wavelength: 350 nm) of the compound (124) of the present invention in a solid state at room temperature using an absolute PL quantum yield measurement apparatus (C9920) manufactured by Hamamatsu Photonics K.K.
  • the emission quantum yield was 0.51.
  • the emission quantum yield (excitation wavelength: 350 nm) of the compound (92) of the present invention in a solid state at room temperature using an absolute PL quantum yield measurement apparatus (C9920) manufactured by Hamamatsu Photonics K.K.
  • the emission quantum yield was 0.28.
  • the emission quantum yield (excitation wavelength: 350 nm) of the compound (1) of the present invention in a solid state at room temperature using an absolute PL quantum yield measurement apparatus (C9920) manufactured by Hamamatsu Photonics K.K., the emission quantum yield was 0.04.
  • the decomposition temperature of the compound (2) of the present invention was measured with a TG/DTA simultaneous measurement apparatus (DTG-60 manufactured by Shimadzu Corp.). As a result of setting the rate of temperature increase to 15° C./min and increasing the temperature at normal pressure under a nitrogen gas atmosphere, 5% decrease in weight was seen at 381° C., and the temperature of 50% decrease in weight was 450° C. or higher. It was demonstrated that the compound (2) of the present invention exhibited very favorable heat resistance.
  • the decomposition temperature of the compound (12) of the present invention was measured with a TG/DTA simultaneous measurement apparatus (DTG-60 manufactured by Shimadzu Corp.). As a result of setting the rate of temperature increase to 15° C./min and increasing the temperature at normal pressure under a nitrogen gas atmosphere, 5% decrease in weight was seen at 400° C., and the temperature of 50% decrease in weight was 450° C. or higher. It was demonstrated that the compound (12) of the present invention exhibited very favorable heat resistance.
  • the decomposition temperature of the compound (39) of the present invention was measured with a TG/DTA simultaneous measurement apparatus (DTG-60 manufactured by Shimadzu Corp.). As a result of setting the rate of temperature increase to 15° C./min and increasing the temperature at normal pressure under a nitrogen gas atmosphere, 5% decrease in weight was seen at 324° C., and the temperature of 50% decrease in weight was 390° C. It was demonstrated that the compound (39) of the present invention exhibited very favorable heat resistance.
  • the decomposition temperature of the compound (41) of the present invention was measured with a TG/DTA simultaneous measurement apparatus (DTG-60 manufactured by Shimadzu Corp.). As a result of setting the rate of temperature increase to 15° C./min and increasing the temperature at normal pressure under a nitrogen gas atmosphere, 5% decrease in weight was seen at 315° C., and the temperature of 50% decrease in weight was 450° C. or higher. It was demonstrated that the compound (41) of the present invention exhibited very favorable heat resistance.
  • the decomposition temperature of the compound (42) of the present invention was measured with a TG/DTA simultaneous measurement apparatus (DTG-60 manufactured by Shimadzu Corp.). As a result of setting the rate of temperature increase to 15° C./min and increasing the temperature at normal pressure under a nitrogen gas atmosphere, 5% decrease in weight was seen at 322° C., and the temperature of 50% decrease in weight was 450° C. or higher. It was demonstrated that the compound (42) of the present invention exhibited very favorable heat resistance.
  • the decomposition temperature of the compound (43) of the present invention was measured with a TG/DTA simultaneous measurement apparatus (DTG-60 manufactured by Shimadzu Corp.). As a result of setting the rate of temperature increase to 15° C./min and increasing the temperature at normal pressure under a nitrogen gas atmosphere, 5% decrease in weight was seen at 324° C., and the temperature of 50% decrease in weight was 450° C. or higher. It was demonstrated that the compound (43) of the present invention exhibited very favorable heat resistance.
  • the decomposition temperature of the compound (47) of the present invention was measured with a TG/DTA simultaneous measurement apparatus (DTG-60 manufactured by Shimadzu Corp.). As a result of setting the rate of temperature increase to 15° C./min and increasing the temperature at normal pressure under a nitrogen gas atmosphere, 5% decrease in weight was seen at 347° C., and the temperature of 50% decrease in weight was 450° C. or higher. It was demonstrated that the compound (47) of the present invention exhibited very favorable heat resistance.
  • the decomposition temperature of the compound (53) of the present invention was measured with a TG/DTA simultaneous measurement apparatus (DTG-60 manufactured by Shimadzu Corp.). As a result of setting the rate of temperature increase to 15° C./min and increasing the temperature at normal pressure under a nitrogen gas atmosphere, 5% decrease in weight was seen at 348° C., and the temperature of 50% decrease in weight was 450° C. or higher. It was demonstrated that the compound (53) of the present invention exhibited very favorable heat resistance.
  • the decomposition temperature of the compound (75) of the present invention was measured with a TG/DTA simultaneous measurement apparatus (DTG-60 manufactured by Shimadzu Corp.). As a result of setting the rate of temperature increase to 15° C./min and increasing the temperature at normal pressure under a nitrogen gas atmosphere, 5% decrease in weight was seen at 364° C., and the temperature of 50% decrease in weight was 450° C. or higher. It was demonstrated that the compound (75) of the present invention exhibited very favorable heat resistance.
  • the decomposition temperature of the compound (76) of the present invention was measured with a TG/DTA simultaneous measurement apparatus (DTG-60 manufactured by Shimadzu Corp.). As a result of setting the rate of temperature increase to 15° C./min and increasing the temperature at normal pressure under a nitrogen gas atmosphere, 5% decrease in weight was seen at 361° C., and the temperature of 50% decrease in weight was 450° C. or higher. It was demonstrated that the compound (76) of the present invention exhibited very favorable heat resistance.
  • the decomposition temperature of the compound (82) of the present invention was measured with a TG/DTA simultaneous measurement apparatus (DTG-60 manufactured by Shimadzu Corp.). As a result of setting the rate of temperature increase to 15° C./min and increasing the temperature at normal pressure under a nitrogen gas atmosphere, 5% decrease in weight was seen at 360° C., and the temperature of 50% decrease in weight was 450° C. or higher. It was demonstrated that the compound (82) of the present invention exhibited very favorable heat resistance.
  • the decomposition temperature of the compound (92) of the present invention was measured with a TG/DTA simultaneous measurement apparatus (DTG-60 manufactured by Shimadzu Corp.). As a result of setting the rate of temperature increase to 15° C./min and increasing the temperature at normal pressure under a nitrogen gas atmosphere, 5% decrease in weight was seen at 358° C., and the temperature of 50% decrease in weight was 450° C. or higher. It was demonstrated that the compound (92) of the present invention exhibited very favorable heat resistance.
  • the analysis results of the compound (1) of the present invention and the comparative compound (formula (C)) are summarized in Table 14. Comparing the emission quantum yields (solid state) of these compounds, they were 0.04 and 0.01, respectively, demonstrating that the compound (1) of the present invention had 4 times higher the emission quantum yield of the comparative compound. Specifically, it was revealed that the emission quantum yield (solid state) of the iridium complex largely depended on the position of substitution of an alkyl group and the introduction of an alkyl group having 2 or more carbon atoms in R a very effectively worked on the improvement in the solid-state emission quantum yield.
  • the compound of the present invention represented by formula (1) or (2) was very thermally stable and exhibited a high emission quantum yield in a solution or in a solid state compared with iridium complexes in which a substituent was not introduced in R a . Furthermore, it was revealed that the emission wavelength could be adjusted by introducing various substituents in the iridium complex of the present invention and by changing the ligand L.
  • the iridium complex of the present invention can be applied to organic electrolumine scent element materials, electrochemiluminescence (ECL) element materials, luminescent sensors, photosensitizers, displays, materials for photographs, laser dyes, dyes for color filters, optical communications, color conversion filters, backlights, illumination, photosensitizing dyes, luminescent probes for cell imaging, various light sources, etc.
  • ECL electrochemiluminescence

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